EP0625563A1 - Esters de polyglycérol utilisés en tant que fluides fonctionnels ou modificateurs de fluides fonctionnels - Google Patents

Esters de polyglycérol utilisés en tant que fluides fonctionnels ou modificateurs de fluides fonctionnels Download PDF

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Publication number
EP0625563A1
EP0625563A1 EP94103952A EP94103952A EP0625563A1 EP 0625563 A1 EP0625563 A1 EP 0625563A1 EP 94103952 A EP94103952 A EP 94103952A EP 94103952 A EP94103952 A EP 94103952A EP 0625563 A1 EP0625563 A1 EP 0625563A1
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Prior art keywords
oil
reaction product
triglyceride
polyglycerol
functional fluid
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EP94103952A
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German (de)
English (en)
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Frank J. Flider
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Calgene Chemical Inc
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Calgene Chemical Inc
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Publication of EP0625563A1 publication Critical patent/EP0625563A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/02—Well-drilling compositions
    • C09K8/32—Non-aqueous well-drilling compositions, e.g. oil-based
    • C09K8/34—Organic liquids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/38—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M109/00—Lubricating compositions characterised by the base-material being a compound of unknown or incompletely defined constitution
    • C10M109/02—Reaction products
    • C—CHEMISTRY; METALLURGY
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    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • C10M111/02—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a non-macromolecular organic compound
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    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • C10M111/06—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a compound of the type covered by group C10M109/00
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/22—Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts
    • C10M2205/223—Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts used as base material
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
    • C10M2207/0225—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups used as base material
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/283—Esters of polyhydroxy compounds
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C10M2207/2835—Esters of polyhydroxy compounds used as base material
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/401—Fatty vegetable or animal oils used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
    • C10M2207/4045—Fatty vegetable or animal oils obtained from genetically modified species used as base material
    • C—CHEMISTRY; METALLURGY
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    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • C—CHEMISTRY; METALLURGY
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
    • C—CHEMISTRY; METALLURGY
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/30—Refrigerators lubricants or compressors lubricants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/32—Wires, ropes or cables lubricants
    • C—CHEMISTRY; METALLURGY
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/34—Lubricating-sealants
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    • C10N2040/36—Release agents or mold release agents
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    • C10N2040/38—Conveyors or chain belts
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    • C10N2040/40—Generators or electric motors in oil or gas winning field
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    • C10N2040/42—Flashing oils or marking oils
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    • C10N2040/50—Medical uses

Definitions

  • This invention relates to biodegradable functional fluids or modifiers for functional fluids such as cutting fluids, hydraulic fluids, chain saw fluids, and H-1 (i.e., food grade) lubricants.
  • functional fluids such as cutting fluids, hydraulic fluids, chain saw fluids, and H-1 (i.e., food grade) lubricants.
  • U.S. Patent No. 4,885,104 discloses metalworking lubricants composed of a reaction product of natural fat or oil, a polyol having from 5 to 15 carbon atoms and a dicarboxylic acid having from 2 to 36 carbon atoms.
  • the natural fat of the composition may be canola oil.
  • a food grade lubricant is disclosed in U.S. Patent No. 5,185,091.
  • the lubricant is preferably composed of decaglycerol monostearate, a triglyceride of a medium chain saturated fatty acids (of 6 to 10 carbon atoms) and glycerol.
  • the ingredients are melted and then kneaded under rapid cooling in order to produce a desired emulsion having a specific dropping point.
  • This product is hydrophilic and substantially insoluble in triglyceride oils.
  • polyglycerol esters can be used as lubricants, and find utility in the textile arts.
  • esters are still relatively low in viscosity and as such, are limited in utility. Higher viscosities may be achieved by using dibasic acids to increase molecular weight, but biodegradability suffers and the economic and environmental considerations for using such lubricants become increasing less attractive.
  • a second drawback as noted above is the insolubility of such products in functional fluids.
  • the Applicant has unexpectedly and surprisingly found a simple solution for improving the viscosity profile and solubility of biodegradable functional fluids without affecting the biodegradability thereof; the solution of the technical problem includes reacting polyglycerols with fatty acids, triglyceride oils or fats and/or blending the resultant esterified polyglycerols with natural fats and oils.
  • the present invention relates to the use of the reaction product of a polyglycerol and either a triglyceride oil or fat, or a fatty acid (or methyl esters thereof) as a high viscostiy functional fluid in mud drilling, as low temperature lubricants, cutting fluids, hydraulic fluids, food grade lubricants or as additives for other functional fluids.
  • the reaction products are preferably blended with a natural oil- or fat-based fluids to control or enhance the viscosity of the natural oil- or fat-based fluids.
  • Glycerol is a polyhydric alcohol, which can be polymerized as disclosed in U.S. Patent No. 3,637,774, herein incorporated by reference. Polymerization may take place in the presence of an alkaline catalyst such as sodium hydroxide, lithium hydroxide, or potassium carbonate in an anhydrous medium, at a median temperature above 200°C. Water, a product of the reaction, is constantly distilled off during the reaction. In such reactions, a family of polyglycerols ranging from diglycerol, having 4 hydroxyl groups, to compounds of the formula (I): wherein n is equal to 1 to 38 or more are formed. It has been found, by correlating the changes in the hydroxyl value and the viscosity of the polyglycerols as they are formed during the course of the reaction, that the reaction may be stopped at any point depending on the degree of polymerization desired.
  • an alkaline catalyst such as sodium hydroxide, lithium hydroxide, or potassium carbonate
  • an anhydrous medium at a median
  • Polyglycerols for n equal to 8 or more are highly viscous and highly polar and thus oil insoluble.
  • the polyglycerols can be esterified with fatty acids or transesterified with methyl esters of fatty acids or triglyceride oils and fats to alter their polarity and their hydrophilic-lipophilic characteristics. It is also observed that as the polyglycerol chain length increases viscosity increases and the hydroxyl value decreases.
  • Viscosities of such larger chain polyglycerols can be further increased by esterification, and because of the molecular length of such larger polyglycerols (e.g., eicosglycerol and docosaglycerol) their viscosity will change (with esterification) without drastically reducing polarity.
  • the resulting polyglycerol ester can vary in viscosity and oil solubility.
  • polyglycerol esters of the present invention can be exploited to produce biodegradable, high viscosity polyglycerol ester functional fluids having varying degrees of polarity; these polyglycerol esters can also be used to enhance the viscosity of other functional fluids.
  • the compositions of this invention are also unique in being formulated from naturally occurring components.
  • the polyglycerol esters of the invention are produced by reacting polyglycerols of formula I above, wherein n is 1 to 100, preferably 1 to 50 and more preferably 1 to 40 with fatty acids, triglyceride oils or triglyceride fats (or methyl esters thereof).
  • the triglycerides reacted with the polyglycerols in accordance with the invention are vegetable oils and animal fats.
  • triglycerides have long chain fatty acids and include, but are not limited to, castor oil, coconut oil, corn oil, cottonseed oil, linseed oil, sesame seed oil, olive oil, palm oil, rapeseed oil, canola oil, safflower oil, soybean oil, peanut oil, sunflower oil, butterfat and lard.
  • the oil is canola oil.
  • Fatty acid reactants include, but are not limited to lauric acid, palmitic acid, oleic acid, linolenic acid, erucic acid, stearic acid, etc.
  • Esterification can take place at any or all of the hydroxy groups on the polyglycerol chain. Depending upon the reaction conditions and the ratio of reactant used relative to the polyglycerol, the number of hydroxyl groups which are esterified varies.
  • the products of the invention have high viscosities at 25°C i.e. between 1000-3000 cSt or greater.
  • the viscosities will only be limited by the degree of esterification and the value of n in formula I.
  • the degree of esterification, or the number of hydroxyl groups esterified is obtained by determining the saponification value (SV) and the hydroxyl value (HV).
  • the saponification value is defined as the number of milligrams of potassium hydroxide neutralized during saponification of one gram of ester.
  • the reaction product of the invention has a saponification value of between 99 and 181 and a hydroxyl value of zero to 387.
  • the saponification value is between about 100 and 169 and the hydroxyl value is between zero and 324.
  • At least 25% of the hydroxyl moieties of the polyglycerol should be esterified.
  • the reaction product depending on its viscosity, can be used as is as a biodegradable lubricant or preferably it is blended with biodegradable triglyceride oils, such as animal fats or vegetable oils, which are currently being used as functional fluids, to improve the viscosity thereof.
  • biodegradable triglyceride oils such as animal fats or vegetable oils, which are currently being used as functional fluids, to improve the viscosity thereof.
  • the reaction product is used in an amount of 5- 95% by weight.
  • polyglycerols of n equal to 4-100 in amounts of between 20-45% by weight and preferably 30% by weight are reacted with a vegetable oil or methyl esters thereof in an amount of 80-55% by weight, preferably 70% by weight, to produce a reaction product which is then blended with a triglyceride oil such as an animal fat or a vegetable oil.
  • a triglyceride oil such as an animal fat or a vegetable oil.
  • the reaction product may be blended with any of the vegetable oils mentioned above or with an animal triglyceride such as butter-fat or lard (which is currently used in metal-working fluids).
  • the triglyceride used as part of the ester reaction product may be the same or may be different from the triglyceride oil or fat which is blended with or improved by the reaction product.
  • a preferred triglyceride oil blended with the reaction product is canola oil.
  • reaction was conducted at 210-250°C for about 20 hours; thereafter the reaction product was treated for two hours at 150°C with 12.5 grams of a synthetic magnesium silicate purifying agent sold under the trademark MAGUSOL HMR-LS, and then filtered.
  • MAGUSOL HMR-LS a synthetic magnesium silicate purifying agent sold under the trademark MAGUSOL HMR-LS
  • Example 1 The reaction of Example 1 was repeated at a temperature of 240-250°C for 6 hours. A canola ester product in a yield of 95% was obtained, before MAGUSOL purification and filtration.
  • Table 1 The characteristics of the reaction products of Examples 1 and 2 are reported in table 1: TABLE 1 Example 1 Example 2 Color 10 Gardner 9 Acid Value 0.9 ---- Saponification value 138.5 143.8 Hydroxyl Value 182.4 177.7 Solubility in canola oil soluble soluble in water dispersible dispersible in mineral oil soluble soluble Viscosity cSt @ 25°C 2421 2424
  • Table 2 is a comparison of the viscosity (cSt) of the product of Examples 1 and 2 to the viscosity of other working fluid esters.
  • cSt viscosity
  • Bi-356 is a proprietary polyol ester of Novamont of Milan, Italy and sold under the trade name Matrol Bi-356. Bi-356 is used in functional fluids because of its high viscosity. EG-20 is eicosyl erucate (a long chain monoester).
  • Decaglycerol was further polymerized to produce a high viscosity polyglycerol.
  • Example 3 The high viscosity polyglycerol of Example 3, which is completely insoluble in oils, was reacted with canola oil to form an oil-soluble product.
  • the high viscosity canola oil ester reaction products of this invention can be used as is, as a food-grade lubricant, a cutting oil, a hydraulic fluid and as an additive for mud drilling fluids and chain saw lubricants.
  • the canola oil ester product can be blended with triglyceride-based functional fluids to alter or enhance the viscosities of such fluids.
  • the reaction of product of Example 1 was blended with canola oil, which is currently being used, with minor amounts of additives, as a hydraulic fluid. Profiles of the viscosity of canola oil and the viscosity of canola oil blended with different amounts of the reaction product of Example 1 are shown for Examples 5-26 in Table 3.
  • reaction product is completely soluble in canola oil and that the viscosity of canola oil can be advantageously altered by the addition of varying amounts of the reaction product.
  • the mixture is also biodegradable.
  • the reaction product can be added to the canola oil by pouring the glycerol ester liquid into canola oil or viceversa either at ambient temperatures or elevated temperatures with stirring.
  • Changes in the polarity and the hydrophilic characteristics of a particular blend or mixture of a reaction product and oil can be made by using as reactants, in the esterification reaction, polyglycerols having greater chain lengths or esters of the triglyceride oil.
  • the methyl ester of a fatty acid, vegetable oil or animal fat can be reacted in a transesterification reaction with a particular polyglycerol to produce a more hydrophobic product than the products of the Examples as reported above.
  • Example 27 The properties of the product of Example 27 are listed below: Hydroxyl Value 155.7 SV 139.5 Viscosity of 35% of product in canola oil 63.5 cSt at 40°C.
  • Example 27 is more hydrophobic and has a lower hydroxyl value than the products of Examples 1 or 2.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • Fats And Perfumes (AREA)
EP94103952A 1993-03-18 1994-03-15 Esters de polyglycérol utilisés en tant que fluides fonctionnels ou modificateurs de fluides fonctionnels Withdrawn EP0625563A1 (fr)

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WO1995026386A1 (fr) * 1994-03-26 1995-10-05 Heriot-Watt University Boue de forage
EP0691315A1 (fr) * 1994-07-08 1996-01-10 Rhone-Poulenc Chimie Procédé de préparation de mélanges aqueux argileux pompables
EP0735127A1 (fr) * 1995-03-31 1996-10-02 Exxon Research And Engineering Company Huile lubrifiante pour un dispositif d'agrafage de couvercles de boîte
WO1996040835A1 (fr) * 1995-06-07 1996-12-19 The Lubrizol Corporation Boues de forage a base d'eau, sans danger pour l'environnement
WO2000029502A1 (fr) * 1998-11-17 2000-05-25 Cognis Deutschland Gmbh Lubrifiant destine a des liquides de forage
WO2010069518A1 (fr) * 2008-12-19 2010-06-24 Cognis Ip Management Gmbh Procédé pour la fabrication d'esters de polyols ayant une qualité de couleur et d'odeur améliorée
EP2285885B1 (fr) 2008-06-02 2015-09-30 Emery Oleochemicals GmbH Agent anti-condensation à base de polyglycérine et d'huiles natives
EP3245864A1 (fr) 2016-05-20 2017-11-22 Akzo Nobel Chemicals International B.V. Agent antibuée

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US6087308A (en) * 1998-12-22 2000-07-11 Exxon Research And Engineering Company Non-sludging, high temperature resistant food compatible lubricant for food processing machinery
SG128420A1 (en) 1998-12-22 2007-01-30 Ricoh Kk Toner container and image forming method and apparatus using the same
US6090761A (en) * 1998-12-22 2000-07-18 Exxon Research And Engineering Company Non-sludging, high temperature resistant food compatible lubricant for food processing machinery
US6182793B1 (en) * 1999-04-13 2001-02-06 Warren Jamison Lubricant delivery system for lubricating rail wheel flanges
US6204225B1 (en) 1999-12-13 2001-03-20 Midwest Biologicals, Inc. Water-dispersible metal working fluid
US6624124B2 (en) 2001-07-13 2003-09-23 Renewable Lubricants, Inc. Biodegradable penetrating lubricant
US6620772B2 (en) 2001-07-13 2003-09-16 Renewable Lubricants, Inc. Biodegradable penetrating lubricant
US6828279B2 (en) * 2001-08-10 2004-12-07 M-I Llc Biodegradable surfactant for invert emulsion drilling fluid
US6884762B2 (en) * 2002-10-28 2005-04-26 Newpark Drilling Fluids, L.L.C. Ester-containing downhole drilling lubricating composition and processes therefor and therewith
US20040241309A1 (en) * 2003-05-30 2004-12-02 Renewable Lubricants. Food-grade-lubricant
US20060211585A1 (en) * 2003-09-12 2006-09-21 Renewable Lubricants, Inc. Vegetable oil lubricant comprising Fischer Tropsch synthetic oils
KR100855112B1 (ko) * 2003-09-12 2008-08-28 리뉴어블 루브리컨츠 인코포레이션 전-수소처리된 합성유를 포함하는 식물유계 윤활유
US7226895B2 (en) * 2004-04-06 2007-06-05 Baker Hughes Incorporated Drilling fluid systems for reducing circulation losses
BRPI0610628A8 (pt) * 2005-04-26 2016-03-08 Renewable Lubricants Inc lubrificante, processo para aprimorar a lubrificação de equipamento
GB201306815D0 (en) 2013-04-15 2013-05-29 Thos Bentley & Son Ltd Functional fluid
CN105331423B (zh) * 2015-12-02 2018-02-16 青岛中科润美润滑材料技术有限公司 一种高氧化安定性环境友好润滑油基础油的制备方法
US20180216022A1 (en) 2017-01-27 2018-08-02 Scott Rettberg System and method for reducing friction, torque and drag in artificial lift systems used in oil and gas production wells
US20190137035A1 (en) 2017-11-03 2019-05-09 Scott Rettberg System and method for reducing friction, torque and drag in artificial lift systems used in oil and gas production wells
CN111139122A (zh) * 2019-11-13 2020-05-12 孙会敏 一种固体脱模剂
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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995026386A1 (fr) * 1994-03-26 1995-10-05 Heriot-Watt University Boue de forage
EP0691315A1 (fr) * 1994-07-08 1996-01-10 Rhone-Poulenc Chimie Procédé de préparation de mélanges aqueux argileux pompables
FR2722131A1 (fr) * 1994-07-08 1996-01-12 Rhone Poulenc Chimie Procede de preparation de melanges aqueux agrileux pompables
EP0735127A1 (fr) * 1995-03-31 1996-10-02 Exxon Research And Engineering Company Huile lubrifiante pour un dispositif d'agrafage de couvercles de boîte
WO1996040835A1 (fr) * 1995-06-07 1996-12-19 The Lubrizol Corporation Boues de forage a base d'eau, sans danger pour l'environnement
WO2000029502A1 (fr) * 1998-11-17 2000-05-25 Cognis Deutschland Gmbh Lubrifiant destine a des liquides de forage
AU756915B2 (en) * 1998-11-17 2003-01-23 Cognis Deutschland Gmbh & Co. Kg Lubricants for drilling fluids
US6806235B1 (en) 1998-11-17 2004-10-19 Cognis Deutschland Gmbh & Co. Kg Lubricants for drilling fluids
EP2285885B1 (fr) 2008-06-02 2015-09-30 Emery Oleochemicals GmbH Agent anti-condensation à base de polyglycérine et d'huiles natives
WO2010069518A1 (fr) * 2008-12-19 2010-06-24 Cognis Ip Management Gmbh Procédé pour la fabrication d'esters de polyols ayant une qualité de couleur et d'odeur améliorée
EP2204358A1 (fr) * 2008-12-19 2010-07-07 Cognis IP Management GmbH Processus de fabrication de polyol-esters avec couleur améliorée et qualité d'odeur
EP3245864A1 (fr) 2016-05-20 2017-11-22 Akzo Nobel Chemicals International B.V. Agent antibuée

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CA2118819A1 (fr) 1994-09-19
US5380469A (en) 1995-01-10
CA2118819C (fr) 1999-07-13

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